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1H, 13C, 17O and 19F NMR spectroscopic study of isomeric ring-substituted monofluoro-(E)-3-phenylpropenals

✍ Scribed by K. Laihia; E. Kolehmainen; P. Mänttäri; R. Kauppinen

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
282 KB
Volume
31
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Isomeric ring substituted monofluoro‐(E)‐3‐phenylpropenals (cinnamaldehydes) were synthesized in order to provide, with the NMR‐active ^19^F nucleus, an insight into the influence of substituents and the transmission of electronic effects between the aromatic ring and the side‐chain. Their ^1^H, ^13^C and ^17^O NMR chemical shifts and their ^n^J(H,H), ^n^J(H,F), ^n^J(C,H) and ^n^J(C,F) values were determined. Generally, the ^n^J(C,F) coupling constants correlate with the length of the coupling route and thus simplify the assignments of the ^13^C NMR spectra. Only the side‐chain carbons C‐2 and C‐3 in the ortho‐substituted compounds showed an exception to this rule. Many long‐range ^n^J(H,F) (n = 4–7) values were easily observed. The ^17^O NMR chemical shift of the carbonyl oxygen in the o‐ and m‐fluoro derivatives show clear substituent effects, whereas p‐fluorocinnamaldehyde shows a value comparable to that of that parent compound.

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